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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
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Chicago
Unavailable
1 Room Left
Hip
DAILY DROP
The Hoxton, Chicago
$168
95%
|
–
West Loop
was on HT
$339
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
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Unavailable
Basic
DEAL
Hampton Inn Chicago Orland Park
$110
93%
|
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West Side
Unavailable
Luxe
L7 Chicago by LOTTE
$189
96%
|
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Loop
was on HT
$319
The former hat factory on the banks of the Chicago River features newly renovated and richly decorated rooms.
Unavailable
1 Room Left
Hip
The Hoxton, Chicago
$216
95%
|
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West Loop
was on HT
$339
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
Unavailable
Solid
DEAL
Hilton Garden Inn Chicago McCormick Place
$159
95%
|
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Loop
was on HT
$249
Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.
Unavailable
Solid
The Royal Sonesta Chicago River North
$183
94%
|
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River North
was on HT
$217
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
Hip
21c Museum Hotel Chicago
$159
95%
|
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Downtown
was on HT
$199
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
Luxe
DEAL
Pendry Chicago
$251
96%
|
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Loop
Bar Pendry's a loungey spot for a late-night glass of wine. Pro tip: seasonal rooftop bar's a must-do in the warmer months.
Unavailable
Luxe
DEAL
The Blackstone, Autograph Collection
$240
91%
|
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Loop
was on HT
$399
There’s a reason it’s been voted one of the best hotels in the city – everything is top-notch, from the views, artwork & modern décor to the nostalgic cocktails.
Unavailable
Solid
Hotel Chicago West Loop, Sure Stay Collection By Best Western
$149
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North Side
was on HT
$179
Bring your furry friends along for the ride. This place is pet friendly.
Unavailable
2 Rooms Left
Solid
Club Quarters Hotel Central Loop, Chicago
$135
85%
|
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Loop
was on HT
$225
Chicago biggies like the Symphony Center & Willis Tower (skydeck is a must!) are within walking distance.
Unavailable
Basic
Majestic Hotel
$135
84%
|
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Lakeview
was on HT
$9,989
On a quiet residential street, providing a relaxing respite in the bustling city.
Unavailable
Solid
Holiday Inn Express & Suites CHICAGO - OAK FOREST
$119
100%
|
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North Side
Unavailable
Basic
DEAL
Level Chicago - River North
$289
93%
|
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Downtown
You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.
Unavailable
Solid
ACME Hotel Company Chicago
$159
93%
|
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River North
was on HT
$269
Playful-meets-industrial-chic design with bold, colorful and artistic accents.
Unavailable
3 Rooms Left
Solid
Level Chicago - Fulton Market
$249
89%
|
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Downtown
was on HT
$309
The outdoor pool takes vacay vibes to new heights.
Unavailable
Basic
Sonesta Simply Suites Chicago Waukegan
$110
82%
|
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Downtown
Suite-style rooms offer up max 'home away from home' vibes.
Unavailable
Solid
DEAL
Club Quarters Hotel Wacker at Michigan, Chicago
$154
84%
|
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Loop
was on HT
$194
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
1 Room Left
Luxe
Loews Chicago Hotel
$229
96%
|
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Magnificent Mile
Head to the rooftop lounge for killer drinks and views (especially if it’s a Navy Pier fireworks night!).
Unavailable
3 Rooms Left
Solid
LEVEL Chicago - Old Town
$259
89%
|
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Downtown
was on HT
$363
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
Luxe
Viceroy Chicago
$299
97%
|
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Gold Coast
was on HT
$355
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
Hip
DEAL
Silversmith Hotel Chicago Downtown
$220
94%
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Loop
was on HT
$290
Urban-luxe design and supersized marble baths keep the cosmopolitan vibe coming.
Unavailable
Solid
DEAL
River Hotel
$154
86%
|
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Loop
was on HT
$234
Excellent authentic Italian resto onsite with fab deep dish pizza (natch).
Unavailable
Basic
DEAL
St. Clair Hotel - Magnificent Mile
$128
82%
|
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Downtown
was on HT
$299
Modern interiors within a cool old building, ideally situated in the heart of the city, steps from the Magnificent Mile.
Unavailable
2 Rooms Left
Hip
Freehand Chicago
$192
83%
|
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River North
was on HT
$217
Style in this 20s-era gem is trendy in a laid-back kinda way. And it’s perfectly placed in a venture-worthy boutique-and-gallery-dotted ‘hood.
Unavailable
Solid
Courtyard by Marriott Chicago at Medical District / UIC
$199
92%
|
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Downtown
Spot-on location for all things medical campus – near UIC Chicago and Rush. PS: Little Italy dining nearby too(!).
Unavailable
Basic
Holiday Inn Hotel & Suites Chicago Downtown
$189
82%
|
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Loop
was on HT
$259
Hit nearby Lou Mitchell’s for breakfast. It’s a Chicago institution and the starting point of Route 66.
Unavailable
Solid
Hampton Inn & Suites Chicago Downtown
$189
88%
|
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Downtown
Killer River North location by the Mag Mile and Riverwalk.
Unavailable
Solid
DEAL
Holiday Inn Chicago Mart Plaza River North
$209
96%
|
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River North
was on HT
$283
All rooms are at least 15 stories above the city. Street noise? Nuh-uh.
Unavailable
Luxe
Omni Chicago Hotel
$344
90%
|
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Magnificent Mile
Ideal Mag Mile address just steps from endless shopping & world-class eateries.
Unavailable
2 Rooms Left
Solid
DEAL
Springhill Suites Chicago O'Hare
$112
92%
|
–
ORD
Catch a free shuttle ride to/from O’Hare airport or to the CTA train station which’ll zip you into the city in no time. (Museums await!)
More amazing deals in:
New York City,
Milwaukee,
Las Vegas - Strip,
San Francisco,
Los Angeles,
Boston,
Miami Beach,
Washington, DC,
Denver,
and tons more!